Conjugated polymers are of great interest for the development of optical and electronic applications. The most investigated conjugated polymers are polyarylenes (such as e.g. poly(thiophene) (PT)), poly(arylene vinylene)s (such as e.g. poly(p-phenylene vinylene) (PPV) or poly(2,5-thienylene vinylene) (PTV)).
There is a continuous interest in polycyclic aromatic compounds, mostly as materials for opto-electronic applications (OLED, OFET, organic photovoltaics, sensors, etc).
The rigid three-dimensional (3D) iptycene units are interesting electron donor which can induce a porous structure into a bulk conjugated polymer.
Several methods have been developed for the synthesis of conjugated polymers containing rigid three-dimensional iptycene units: Poly(arylene vinylene) derivatives containing iptycene moieties (and more specifically triptycene units) were reported by T. Swager (U.S. Patent publication No. 2006/0073607A1 and JACS 2004, vol. 126, p. 452). These polymers were produced in a “one-pot” synthesis by polycondensation of para-dihalomethyl-substituted triptycene derivatives. Polymers containing iptycene units were also reported by H. Becker (U.S. Pat. No. 6,605,693) as electroluminescent materials. A list of particular methods for the preparation of poly(triptycenyl vinylenes) is given in U.S. Pat. No. 6,605,693 (e.g. polycondensation of para-dihalomethyl-substituted triptycene, Wessling precursor route, Homer and Wittig polymerization, Knoevenagel reaction).
A homopolymer according to formula (XIII) has been disclosed in US 2006/0073607.

This homopolymer is obtained by a direct route. Other iptycenylene vinylidene derivatives are disclosed in U.S. Pat. No. 6,605,693, which are copolymers comprising a high amount (75% or more) of phenylene vinylidene co-monomers. Those last polymers have also been synthesized according to a direct route. The synthetic scheme used so far in the prior art for synthesizing iptycenylene vinylene derivatives does not permit synthesis of poorly soluble iptycenylene vinylene derivatives. For instance it does not permit the synthesis of homopolymers of unsubstituted iptycenylene vinylidene of high molecular weight (e.g. above 10000 daltons) or copolymers of high molecular weight (e.g. above 10000 daltons) comprising a large amount of unsubstituted iptycenylene vinylene derivatives.
There is still a need in the art for a method versatile enough to permit the synthesis of a broad range of soluble or insoluble homo- and copolymers of iptycenylene vinylidene monomers. There is also a need in the art for new monomers and precursor polymers that can be converted into conjugated iptycenylene vinylidene polymers.